Water → 6-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-one

HRID 1947490Notes

Reaction equation

HRID 1947490 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[OH:18][C:19]1[CH:28]=[CH:27][C:22]2[C:23](=[O:26])[CH2:24][O:25][C:21]=2[CH:20]=1.O>CN(C=O)C>[C:1]([Si:5]([CH3:7])([CH3:6])[O:18][C:19]1[CH:28]=[CH:27][C:22]2[C:23](=[O:26])[CH2:24][O:25][C:21]=2[CH:20]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 234389036-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl-chloro-dimethyl-silane (12.6 g, 83.9 mmol) in DMF (120 mL) was added DIEA (18.4 g, 24.9 mL, 142.7 mmol) and the mixture was stirred (rt, 0.5 h). The reaction mixture was treated with 6-hydroxy-benzofuran-3-one (12.0 g, 79.9 mmol) and stirred (rt, 0.25 h). The reaction mixture was treated with water (100 mL) to form a solid. The solid was filtered to afford the title compound as a yellow solid (20.4 g, 98%). MS (ESI): mass calcd. for C14H20O3Si, 264.1; m/z found, 265.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.55 (d, J=8.4, 1H), 6.57 (dd, J=8.5, 2.0, 1H), 6.51 (d, J=1.9, 1H), 4.60 (s, 2H), 0.99 (s, 9H), 0.26 (s, 6H).

Workup

  1. stirringstirred (rt, 0.25 h)
  2. customto form a solid
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-013675b887594bdfb49c674f217c52f7
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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